1: N-methyl formanilide; POCl3; 1,2-dichloro-benzene 2: N2H4+H2O; KOH; diethylene glycol View Scheme

Nafion-H in o-xylene T=160°C; 1 h;

1: 82 percent / TiCl4 / CH2Cl2 / 2 h / 20 °C 2: 85 percent / AlH2Cl / diethyl ether / 3 h / Heating 3: 87 percent / Nafion-H / o-xylene / 1 h / 160 °C View Scheme

1: 85 percent / AlH2Cl / diethyl ether / 3 h / Heating 2: 87 percent / Nafion-H / o-xylene / 1 h / 160 °C View Scheme

1: 80 percent / AlCl3 / CH2Cl2 / 2 h / Ambient temperature 2: 82 percent / TiCl4 / CH2Cl2 / 2 h / Ambient temperature 3: N2H4*H2O / toluene; bis-(2-hydroxy-ethyl) ether / 1 h / Heating 4: KOH / bis-(2-hydroxy-ethyl) ether / 3 h / 180 °C 5: 78 percent / Nafion-H, toluene / 12 h / Heating View Scheme

1: N2H4*H2O / toluene; bis-(2-hydroxy-ethyl) ether / 1 h / Heating 2: KOH / bis-(2-hydroxy-ethyl) ether / 3 h / 180 °C 3: 80 percent / AlCl3 / CH2Cl2 / 2 h / Ambient temperature 4: 82 percent / TiCl4 / CH2Cl2 / 2 h / Ambient temperature 5: N2H4*H2O / toluene; bis-(2-hydroxy-ethyl) ether / 1 h / Heating 6: KOH / bis-(2-hydroxy-ethyl) ether / 3 h / 180 °C 7: 78 percent / Nafion-H, toluene / 12 h / Heating View Scheme

1: 38 percent / KOH, NaBH4 / benzene; ethanol / 6 h 2: MCPBA / CHCl3 / 6 h / -5 °C 3: 6.1 percent / 480 °C / 0.8 Torr 4: 78 percent / Nafion-H / toluene / 12 h / Heating View Scheme

Nafion-H 12 h; Heating;

1: 90 percent / TiCl4 / CH2Cl2 / 3 h / Ambient temperature 2: N2H4*H2O / toluene; bis-(2-hydroxy-ethyl) ether / 1 h / Heating 3: KOH / bis-(2-hydroxy-ethyl) ether / 3 h / 180 °C 4: 80 percent / AlCl3 / CH2Cl2 / 2 h / Ambient temperature 5: 82 percent / TiCl4 / CH2Cl2 / 2 h / Ambient temperature 6: N2H4*H2O / toluene; bis-(2-hydroxy-ethyl) ether / 1 h / Heating 7: KOH / bis-(2-hydroxy-ethyl) ether / 3 h / 180 °C 8: 78 percent / Nafion-H, toluene / 12 h / Heating View Scheme

1: KOH / bis-(2-hydroxy-ethyl) ether / 3 h / 180 °C 2: 80 percent / AlCl3 / CH2Cl2 / 2 h / Ambient temperature 3: 82 percent / TiCl4 / CH2Cl2 / 2 h / Ambient temperature 4: N2H4*H2O / toluene; bis-(2-hydroxy-ethyl) ether / 1 h / Heating 5: KOH / bis-(2-hydroxy-ethyl) ether / 3 h / 180 °C 6: 78 percent / Nafion-H, toluene / 12 h / Heating View Scheme